1924-28-3Relevant articles and documents
TRANSITION METAL-PROMOTED REACTIONS. X. PENTACARBONYLIRON-PROMOTED REDUCTIVE COUPLING OF BENZOYL CHLORIDE IN HALOBENZENES
Luh, Tien-Yau,Lee, Kim Sze,Tam, S. W.
, p. 221 - 224 (1983)
Reductive coupling of benzoyl chloride to give trans- and cis-α,α'-stilbenediol dibenzoates is found to be promoted by pentacarbonyliron.The mechanism is briefly discussed.
Methylsulfinyl (Dimsyl) anion as umpolung catalyst for the chemoselective cross-benzoin reaction of α-diketones with aldehydes
Bortolini, Olga,Fantin, Giancarlo,Ferretti, Valeria,Fogagnolo, Marco,Giovannini, Pier Paolo,Massi, Alessandro,Pacifico, Salvatore,Ragno, Daniele
, p. 3244 - 3252 (2013/12/04)
The hitherto unreported ability of the methylsulfinyl carbanion (dimsyl anion) to generate acyl anion equivalents is described. The dimsyl anion, in fact, efficiently catalyzes chemoselective intermolecular cross-benzoin condensations of diaryl α-diketones (benzils) with various aromatic and aliphatic aldehydes to give the corresponding aryl-aryl and aryl-alkyl benzoin benzoates in an atom-economic fashion. The dimsyl anion acts as an environmentally friendly alternative to the toxic cyanide anion and it is obtained by in situ deprotonation of dimethyl sulfoxide (DMSO) solvent with a catalytic amount of a strong base, potassium tert-butoxide (t-BuOK) the optimal promoter. The assumption that the methylsulfinyl carbanion is the active catalyst in the title transformation is supported by electrospray ionization mass spectrometry (ESI-MS) experiments. Copyright
Transformation of acid chlorides into aldehydes by reduction of in-situ formed acyltributylphosphonium ions with zinc-copper couple or zinc
Maeda, Hatsuo,Maki, Toshihide,Ohmori, Hidenobu
, p. 2247 - 2250 (2007/10/02)
Transformation of acid chlorides into the corresponding aldehydes without over-reduction to alcohols was effectively achieved by the reduction of acyltributylphosphonium ions, formed in-situ from the chlorides and tributylphosphine in CH3CN, with Zn-Cu couple or Zn in the presence of CH3SO3H under an N2 atmosphere.
Neue Synthesen und Reaktionen ungesaettigter Heterotitanacyclen
Duerr, Stefan,Hoehlein, Udo,Schobert, Rainer
, p. 89 - 96 (2007/10/02)
Dicarbonyltitanocene reacts chemoselectively with difunctional carbonyl compounds such as 1,2-diketones and 1,4-diketo-2-enes, with α-ketothioketones, α-ketoimines and azodicarbonic esters and -amides to yield the corresponding, mostly new, heterotitanacycles that are capable of a lot of a useful follow-up reactions.These chelate complexes, containing three to four heteroatoms, allow the substitution of the entire titanocene fragment by carbon (formation of vinylenic carbonates and the thia-derivatives of these) or by further heteroatoms like boron or phosphorus(formation of boroles and phosphonic acid derivatives), thus retaining the cyclofunctionality.Alternatively, some of the new chelate complexes can be readily C-C-chain-lengthened via a deprotonating/alkylating sequence, leaving the metallacycle unaffected.